Ethambutol

Title: Ethambutol
CAS Registry Number: 74-55-5
CAS Name: 2,2¢-(1,2-Ethanediyldiimino)bis-1-butanol
Additional Names: (+)-2,2¢-(ethylenediimino)di-1-butanol; d-N,N¢-bis(1-hydroxymethylpropyl)ethylenediamine; EMB
Molecular Formula: C10H24N2O2
Molecular Weight: 204.31
Percent Composition: C 58.79%, H 11.84%, N 13.71%, O 15.66%
Literature References: Prepn: Wilkinson et al., J. Am. Chem. Soc. 83, 2212 (1961); eidem, J. Med. Chem. 5, 835 (1962). Pharmacology: Kulig et al., Diss. Pharm. Pharmacol. 23, 463 (1971), C.A. 76, 81239d (1972). Comprehensive description: C. S. Lee, L. Z. Benet, Anal. Profiles Drug Subs. 7, 231-249 (1978). Mechanism of action: W. H. Beggs in Antibiotics vol. 5(pt. 1), F. E. Hahn, Ed. (Springer-Verlag, New York, 1979) pp 43-66.
Properties: mp 87.5-88.8°. [a]D25 +13.7° (c = 2 in water). Sol in chloroform, methylene chloride; less sol in benzene; sparingly sol in water.
Melting point: mp 87.5-88.8°
Optical Rotation: [a]D25 +13.7° (c = 2 in water)
Derivative Type: Dihydrochloride
CAS Registry Number: 1070-11-7
Trademarks: Dexambutol (L'Arguenon); Ebutol (Kaken); Etibi (Gerot); Etapiam (Piam); Myambutol (Wyeth); Mycobutol (Cadila); Sural (Chinoin); Tibutol (Bracco)
Molecular Formula: C10H24N2O2.2HCl
Molecular Weight: 277.23
Percent Composition: C 43.32%, H 9.45%, N 10.10%, O 11.54%, Cl 25.58%
Properties: mp 198.5-200.3°; also reported as mp 201.8-202.6°. [a]D25 +7.6° (c = 2 in water). Sol in water, DMSO; sparingly sol in ethanol; difficultly sol in acetone, chloroform.
Melting point: mp 198.5-200.3°; mp 201.8-202.6°
Optical Rotation: [a]D25 +7.6° (c = 2 in water)
Derivative Type: Mixture with isoniazid methane sulfonate
CAS Registry Number: 41663-50-7
Additional Names: (+)-2,2-(Ethylenediimino)dibutanol diisoniazide methanesulfonate; isobutol
Trademarks: Isoetam (Ferrer)
Literature References: Prepn: C. Ferrer-Salat et al., BE 753862; US 3718655 (1971, 1973 both to Lab. Ferrer).
Properties: White powder, crystallizes as needles, mp 121-122° (dec). Sol in water, methanol, N,N-dimethylformamide. Insol in ethanol, ethyl ether, chloroform. uv max: 265 nm. [a]D20 +3° (c = 5% in water). LD50 in mice (g/kg): 2.800 orally; 2.210 i.p. (Ferrer-Salat).
Melting point: mp 121-122° (dec)
Optical Rotation: [a]D20 +3° (c = 5% in water)
Absorption maximum: uv max: 265 nm
Toxicity data: LD50 in mice (g/kg): 2.800 orally; 2.210 i.p. (Ferrer-Salat)
Therap-Cat: Antibacterial (tuberculostatic).
Keywords: Antibacterial (Tuberculostatic).
Ethamivan Ethamsylate Ethanearsonic Acid Ethanethiol Ethanolamine

Ethambutol
Ethambutol.svg
Ethambutol substance photo.jpg
Ethambutol ball-and-stick.png
Identifiers
CAS number 74-55-5 YesY
PubChem 14052
ChemSpider 13433 YesY
UNII 8G167061QZ YesY
EC number 200-810-26
DrugBank DB00330
KEGG D07925 YesY
MeSH Ethambutol
ChEBI CHEBI:4877 YesY
ChEMBL CHEMBL44884 YesY
ATC code J04AK02
Jmol-3D images Image 1
Properties
Molecular formula C10H24N2O2
Molar mass 204.31 g mol−1
Appearance White crystals
Odor Odourless
log P −0.291
Pharmacology
Routes of
administration
Oral
Metabolism Hepatic
Elimination
half-life
3–4 hours
Protein binding 20–30%
Excretion Renal
Pregnancy
category
B
Related compounds
Related compounds
  • ethylenediamine
  • TMEDA
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Ethambutol (commonly abbreviated EMB or simply E) is a bacteriostatic antimycobacterial drug prescribed to treat tuberculosis.[2] It is usually given in combination with other tuberculosis drugs, such as isoniazid, rifampicin and pyrazinamide.

It is sold under the trade names Myambutol and Servambutol.